Fallon Files: Jimmy Cedes Control to Taylor Swift

Finally, his lack of preparation works in someone’s favor

Todd Owyoung/NBC
She's A Mastermind
Fallon Files

Welcome to the Fallon Files, a weekly-ish series chronicling only the lowest lows of The Tonight Show Starring Jimmy Fallon.


Taylor Swift does not usually do a lot of press when it comes to her album releases. If fans are extremely lucky, she will sit down with a journalist for a profile, but those are few and far between. The next best thing is a late-night talk show appearance, where we can only hope that the host has (at the bare minimum) listened to the album and is prepared to discuss it. All signs point to Jimmy not having done that in preparation for Swift’s appearance on the Tonight Show on Monday. Luckily for Swift, that actually seems to work in her favor.

Swift, in case it wasn’t obvious from at least the past eight years of her career, loves to control her own narrative. How successful she is in that endeavor may vary, but it is what she strives for. With Jimmy, she’s completely in charge — she can just go in and say whatever she wants, because it’s not like he is going to ask her something that throws her off (he’s not Stephen Colbert). So on her Monday night appearance she just talked and talked and talked while Jimmy laughed and laughed and laughed.

He did occasionally ask a question, though. I will compile everything he asked her in their first segment, and while you’re reading the list, I want you to imagine that, in front of you, you have the world’s most famous pop star, who has just released what might be her most confessional and hyped album yet. Are these the questions you would ask?

  • “Is it a lot? Are you excited? Are you freaking?”
  • “You said a lot of this album is made out of stories, out of thirteen sleepless nights throughout your life… Do you just get up and go [gasp] in the middle of your sleep or, you know, record something on your phone or jot something down?”
  • “Do you know ‘Mastermind’ is gonna be the 13th track?”
  • “Is [Dylan O’Brien] a drummer?”
  • “Did you know [O’Brien] before the film All Too Well?”
  • “Are we talkin’ sooner than later?” (in regards to a tour)
  • “Can you… see how many cats you can name in 30 seconds?”

If I’m being generous, precisely one of these is almost enough to qualify as a good question. The rest are, respectfully, boring, but I think that’s just what Swift wants. In the late-night landscape, Jimmy is the most amenable host for a guest who knows exactly what they’re going to say and how they’re going to say it. The less Jimmy opens his mouth, the better, and Swift can talk about what Midnights means to her and the magic of touring and the process behind making the album on her own terms.

Take, for example, the two questions about actor Dylan O’Brien. Why would Jimmy use any of his precious Taylor Time to talk about her least famous collaborator, especially when Lana Del Rey and Zoë Kravitz are also credited on the album? Well, if you’ve been paying attention to Swift and know that she is campaigning for an Oscar for All Too Well: The Short Film, which stars O’Brien. Under the guise of incompetence, Jimmy actually teed Swift up to talk about the amazing performance her star gave under her potentially award-worthy direction.

This is Jimmy’s whole thing. He is not going to put in the work, but if you — or, more realistically, your publicist — are smart enough, you can make that work for you. The reason that so many of his interviews are bad is because he isn’t really hosting the show, so it falls to the guest to take the lead. This works out best for celebrities like Swift, who have a laundry list of points they want to hit during their appearance.

So congratulations to Ms. Swift for doing what so few people know how to do: making Jimmy work for her. She talked about the album, she announced the tour, she campaigned for an Oscar, and when she listed all the cat breeds she knew, it was only kind of weird. That’s about as successful as a Tonight Show appearance can be.